


Pressing Your Luck

by joyfilled_noise



Category: Arrow (TV 2012)
Genre: Bratva, F/M, Kid Fic, Modern AU
Language: English
Status: In-Progress
Published: 2017-02-14
Updated: 2018-04-05
Packaged: 2018-09-24 07:22:59
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 14,294
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9710909
Author URL: https://archiveofourown.org/users/joyfilled_noise/pseuds/joyfilled_noise
Summary: Felicity Smoak is down on her luck.  She heads to an underground casino to make some quick cash but ends up running into an old flame.  Is her luck starting to change or has it finally all run out?





	1. Chapter 1

**Author's Note:**

> Enjoy!

Felicity Smoak was down on her luck. It wasn't like she needed luck in the underground casino that she had found herself in but it definitely wouldn't have hurt. Just when she was about to call it a night and cash in her chips she found herself being blocked by an impressively large man.

"Excuse me ma'am, the boss would like to see you." 

Felicity tried not to panic; at both being called ma’am and being caught counting cards. She had been betting under the tables limits and losing periodically to not attract attention but not doing a good enough job apparently. Felicity plastered what she hoped would be an innocent smile on her face.

"Is there something wrong? I was just headed out."

"Sorry ma’am, the boss isn't always forthright, he just requested your presence. I tend not to question him when he's in one of his moods." 

Felicity felt a pressure on the small of her back as he guided her away from the blackjack table, "What kind of mood are we talking about? Good mood? Bad mood? Feeling frisky? Wait, no. I'm not being propositioned am I? Because I have too much on my plate right now to start working in the sex trade industry. Though they might pay better than my current employer...not that I'm seriously thinking about becoming a prostitute!" Felicity paused for a moment closing her eyes and taking a deep breath, "Sorry, sometimes my words run away and it takes a bit for my brain to catch up. What I was trying to ask was, am I in any danger?" Felicity stopped once more to look at the gentleman who was now leading her down a long hallway at the back of the casino hoping to see a note of reassurance in his eyes, anything to tell her that she was safe. 

"I really don't know miss. I'm sorry."

They walked the rest of the way down the hall in silence as the anxiety in the pit of Felicity's stomach started to grow, along with the sweat on her palms. As the man opened the door to a dimly lit office, Felicity wiped her palms over her red, one-shouldered cocktail dress and took a deep breath and stepped over the threshold. 

"Have a seat Miss Smoak." A man sitting behind a desk in the corner stated. He was cloaked in shadows so Felicity couldn't tell what the man looked like but there was a familiarity to him that she couldn't quite place. "That will be all Diggle."

The man who had escorted her to the office looked at the boss and then back to Felicity, staring at her for a long moment before he turned around and shut the door behind him. 

"Have a seat Miss Smoak." Felicity shook her head out of the daze she had found herself in, a sinking feeling of deja vu came over her. She could just make out the man gesturing to one of the two chairs directly in front of his desk. 

"Umm. I think I'd rather stand. Over here. Away from you." Felicity began playing with her hands in front of her trying to relieve some of the nervous tension radiating throughout her entire body. "Not that I don't trust you. Wait. I don't trust you, not that you aren't a trustworthy person it's just this is an underground casino and I'm in the owner's office. That doesn't bode well for me and I've seen too many movies and this situation never fairs to well for the actor in my position. The phrase 'She'll be sleeping with the fishes' comes to mind." 

A breathy chuckle comes from the man in the corner and Felicity can't help but pop her head up from the design of the carpet she had been so focused on before. This may have been the first time Felicity ever wished she was an owl or some other nocturnal creature because she knew deep in her bones that this was not the first time she had heard that laugh. 

"I would never hurt you, Felicity."

In a flash, the warm churning of nerves that has been playing throughout Felicity's body during this conversation is replaced by an eerie chill. She would recognize the way that man said her name anywhere, even though she hadn't heard it in years. Just as the epiphany hits, the man reaches for the lamp that sits on the corner of his desk, finally illuminating his handsome features. Felicity stares at him, letting the time pass as she slowly gets a grasp on what she is seeing.

In a breath, barely audible, Felicity finds herself taking a step closer, "Oliver."

\----------------

Felicity is sitting at the bar waiting for her mother to get off work slowly making her way through her second Shirley Temple while scrolling through her phone looking at a tech article her college roommate had messaged her. She was so engrossed in what she was reading that she didn't even notice when the bar stool next to her became occupied. 

Someone near her cleared their throat but instead of looking up Felicity reached for her drink and continued to read.

Again someone cleared their throat, this time longer and sounding much more disgruntled. She looked up to see an attractive man sitting next to her openly starring, a smirk, and a look of desire could clearly be seen behind his blue eyes. 

Slightly annoyed that this man had interrupted her and also used to being hit on by men of all ages while sitting at this same bar waiting for her mother, Felicity was well versed in avoidance tactics. Though, none of the previous men that had hit on her had such broad shoulders and muscular arms under a black t-shirt that she found herself wanting to tear off his body. Felicity shook her head trying to reign in her libido and caught the attention of the bartender, Jerry.

"Jerry! This gentleman seems to have a serious mucus issue. Can you get him a water please?" Felicity turned and gave the handsome gentleman a tight lipped smile and turned back to her phone.

"Here you go sir. And if you feel the need to cause this young lady any more trouble I will have security escort you out. Understood?" 

Felicity peeked over at the man sitting next to her as subtly as possible to see him still unashamedly staring at her but now a small smile played at the corner of his lips, amusement clearly shining in his eyes.

"I wouldn't dream of bothering the beautiful lady." After taking a sip of his water the man stands and finally looks at Jerry who is standing in front of them with his arms crossed and a frown on his face. The man turns back to Felicity slowly invading her bubble before whispering in her ear, "Thanks for the drink, but I can think of other ways for you to quench my thirst." His breath is hot on her ear and she fights the urge to lean into this handsome stranger, instead she just closes her eyes as she feels him leave a lingering kiss just on the apex of her jaw just below her earlobe. She thinks he turns away before he sees her shiver at the contact. 

After he leaves, Felicity is frozen in her seat trying to figure out what just took place. She looks up at Jerry and then back in the direction the stranger had disappeared to and then back at Jerry. Felicity frowns, and then tilts her head to the side, "Did that really just happen?" Her voice sounds breathy even to her own ears and even though she's a genius, Felicity is having a difficult time figuring this problem out, even though she's not quite sure she has a problem. Yet.


	2. Chapter 2

**Notes for the Chapter:**

> Thank you so much for taking the time to read my story. Enjoy!

"Oliver."

She can't help but stare at the man she hasn't seen in five years, noting the stupid smirk on his face she recognizes from the first time that she ever saw him. He barely looks any different, time has been annoyingly good to him. The lights are low and she's scared to look at him too closely, knowing the feelings she had for him that she placed securely in a box locked deep within the darkest corners of her heart could re-emerge if she gets even the smallest bit invested. 

He stands from his seat and slowly walks in front of his desk and leans back against it and crosses his arms. He appears to be the calm, cool, and collected version she remembers from whenever she watched him do business. 

"You're unusually quiet this evening." His voice is soft and his head tilts to the side like he's trying to figure out a puzzle. Felicity pushes out a huff of air through her nose, like she was ever the big mystery in their relationship or lack of relationship, or whatever term they had ended up deciding on. 

With that one thought her mind quickly snaps into focus and the walls she erected around her life and her family's life quickly fall into place. "Well, I never wanted to see you again. So imagine my surprise." Oliver always had terrible tells or at least she had learned to read him because words were never his strong suit, so she sees the tick in his jaw and the slight narrowing of the eyes even though he's trying to hide it from her. Maybe to push his buttons, or just to fortify her castle walls with a moat she belatedly adds, "And disappointment."

Anyone could feel the tension filling Oliver's body at the last prod and he looks to the ceiling in an attempt to regain composure. She's seen him do it countless times when they fought so she knows that his composure never lasts long before he starts raising his voice and invading her bubble hoping she'll back down, though she never did. She steels herself up knowing she won't back down now but also knowing that being in close proximity to Oliver will take just as much restraint on her end as it does on his. 

He looks to the ground and then turns around and crosses back behind his desk again. Felicity's brow crinkles in slight confusion, this is not what she expected. She was prepared for anger and loud voices and pushing each other’s limits to the edge. Now he's sitting behind his desk with his fingers linked together atop the desk she sees the cold, hard mask that he never used with her before. She's seen him use it on countless others, but never her. It's then when she starts to feel the nervousness that she thought she was rid of slowly slink its way back into her gut. 

"If that's the way you want to play this." There's a slight pause as if he's hoping she'll rescind her previous statement but she has too much to lose so she straightens her shoulders, stands a little taller, and looks him in the eyes attempting to mirror his own hard mask. "Have a seat Miss Smoak."

Felicity debates whether she'll give into the command when he starts in, "Miss Smoak, we're about to talk business. The door is being guarded. You should make yourself comfortable." She really wants to defy his order but her stilettos are starting to feel like the worst decision she's made tonight when there are so many other decisions she should be regretting, so she pulls the chair back and sits. 

"I don't think we have any business. We wrapped that up years ago." Felicity knows she's egging him on, hoping that he'll drop the mask that he's using with her but it seems to only solidify.

"Are you aware of the penalty for counting cards in a casino owned by the Bratva, Miss Smoak?" 

Felicity's eyes widened and a small gasp escapes her lips before she can stop it. "You wouldn't."

"You're right Miss Smoak, I wouldn't. I made a promise to you long ago that I wouldn't hurt you and I won't, but that doesn't mean I can't have someone else take care of my dirty work."

Felicity tries to control the tears that are welling up in her eyes, trying to figure a way out of this mess she has found herself in. She wants to believe he would never hurt her, but that was a long time ago, "You also promised you would always take care of me too." It sounds bitter and slightly choked up and she can't look him in the eyes as she says it but she's passed the point of caring. The last week had been exhausting and she's fairly certain that all of the adrenaline she did have has now been sapped out of her body.

The room is quiet for a moment and she can hear the distant noises from the casino. It's late in the evening and the drinks have been flowing freely for many of the patrons for hours now. She hears Oliver take a deep breath and knows she can't bare to look at his face, terrified of whether she will see her Oliver there or the mask. In her current, state she can't decide which one is worse. 

"I would have too." The tone is matter of fact but within it, there are a thousand things left unsaid. "And since I'm feeling nostalgic tonight you may leave with all your fingers. You'll be allowed to take half of your winnings but you'll also be banned. You'll have to find a different casino to count cards because it certainly won't be here. Goodnight Miss Smoak. Diggle will escort you out." 

After his directive, Felicity's eyes found their way back to his face but he had already turned to face his computer, and she couldn’t tell if he was truly engrossed or pretending to be distracted. Standing and walking towards the exit at his clear dismissal, Felicity couldn't help but pause at the door before she left the room, "I am truly sorry, Oliver."

Without looking away from his computer Oliver replied, "Shut the door on your way out."

\--------------------------------------------------------------------------------------------------------------------------

Oliver isn't quite sure what brings him back to the Pink Flamingo. Yesterday, he was clearly dismissed by a young woman who couldn't have been much older than twenty who he had shamelessly flirted with, but Oliver was an incredibly good liar, especially to himself. His eyes glide over the casino to check for threats and once he knows he's safe his eyes beeline for the bar. There she is in a pink summer dress with a yellow cardigan over top showing off a tiny bit of cleavage, just enough to set Oliver's skin on fire. After being dismissed yesterday Oliver couldn't help but see if he could win a bet he set against himself; he wanted to see how fast she would fall into bed with him. Now, though, he just needed to know what her skin tasted like. 

He slowly makes his way to the bar, glancing at the bartender noting it's a different one from the day before. This one is younger and if Oliver's intuition is correct he's new to the place so he heads over a distance away from the feisty blonde and catches the bartender's attention. 

"I'll have a vodka, neat."

"Sure thing sir." 

"What do you know about the blonde at the end of the bar?" Oliver goes for casual, but can't mask the predatorial inflection to his own ear. 

"I don't know, some nerd whose mom works here. Sits at the bar taking up space." The bartender gives Oliver a once over, "If you're trying to get into her pants it's not gonna work. I tried a week ago when I first started and she wasn't havin' any of it. Now she doesn't even order anything, just takes up space." 

Oliver smirked over his tumbler and looks the bartender in the eye, "I'll keep that in mind." He is about to make his way over to her before he turns back to the bartender, "Can I also get a Shirley Temple?" 

The bartender quickly complies to the request and Oliver tips generously dropping a hint for the bartender to stay towards this end of the bar. Oliver grabs the Shirley Temple strides over to the blonde sits on the stool next to her and slides the drink under her nose obscuring her line of sight to the book she's engaged in.

She jumps in her seat and her eyes follow his hand up to the clear amusement written all over Oliver's face. "You," she breathes. 

The smirk only gets bigger, "Is that your way of saying you miss me?" 

She shakes her head and Oliver can see the exact moment she turns back into the feisty woman he met yesterday, "No. But if it works for you, go with it." She shoves the drink back over to him and returns to her reading. 

Oliver's hand comes up to the one holding her book and mindlessly draws patterns into the back of her hand, when she doesn't pull away he takes this as a good sign and continues talking. "I bought the drink for you. Shirley Temple, right?"

The girl looks over her book towards him and arches an eyebrow.

"I'm fairly observant and you looked thirsty." His eyes are intense on hers and he halts the patterns on her hand to slide the drink back over to her, never breaking eye contact. 

Her eyes widen marginally and before he knows what's happen a string of words are tumbling out of her mouth, "No. No, no, no, no, no. I grew up in Vegas, my mother has ingrained in me to never take drinks from strangers. Even hot strangers, with gorgeous blue eyes, and stubble, and muscles." She shakes her head, clearly in an attempt to get back on topic, "But that's not the point. You probably spiked it. Not to put you in a box of men who take advantage of women but yesterday you kissed me and you don’t even know my name. And the hand thing you just did. I'm fairly certain that means you want to have sex. With me. Which doesn't totally make sense, because as previously mentioned you’re a super hot stranger and I'm just an MIT student who clearly has nerd written all over her." She stops and looks at him and her eyes widen even bigger than before, "But I know people here, like security type people here, and I know I kind of insulted you but you're also way bigger than me and not in the fat way but in the built way, like muscles that you clearly know how to use." She closes her eyes tight and grimaces. 

Oliver just stares at her for a minute before he lets out a breathy chuckle and sees the blonde open one eye while keeping the other tightly closed. He ducks his head to get control of his laughter and when he looks back up at her there is still amusement written in his features, but also a bit of determination. 

"I was just looking to return your favor from yesterday. And a name. A name of the girl who turned me down so extraordinarily yesterday."

The other eye opens slowly and her brow furrows as she clearly debates what name to give him, if any. With great trepidation, she closes the book in her hands and holds her right hand out in front of him, "Felicity."

The smile that lights up his face is genuine as he takes her hand in his, "Oliver, a pleasure to meet you." Oliver slowly gets up from his stool and reluctantly releases her hand. He takes one more sip of his vodka before he turns back to her where she is openly staring at him with a puzzled expression. Once again he slowly invades her bubble and her eyes widen and he hears her breath hitch when it looks like he's going in for her lips but at the last second he turns to her ear like yesterday, "Felicity, I need my women cognizant when they're in bed with me so they know just how much pleasure I can give them." He smiles as she shudders. He’s tempted to touch her again but doesn’t want to pressure her and wants to play this smart. She seems interested but she’s not like his usual bed guests fawning all over him. So Oliver lingers, watching the blush rise up in her cheeks. 

"I'll see you tomorrow Felicity." He turns around and exits the casino without looking back. He's about 80 percent certain she'll fall into bed with him because Oliver rarely loses a bet, even against himself. He rolls his eyes at his own internal dialogue, "The house always wins," as the doors slide open to the Vegas heat.

**Notes for the Chapter:**

> All publicly recognizable characters, settings, etc. are the property of their respective owners. The original characters and plot are the property of the author of this story. The author is in no way associated with the owners, creators, or producers of any previously copyrighted material. No copyright infringement is intended.


	3. Chapter 3

**Notes for the Chapter:**

> Thank you so much for reading my story, enjoy!

There's a knock at Oliver's office door and he knows who it is before he even calls for them to enter. John Diggle, Oliver's enforcer and closest confidant, walked in and Oliver quickly sees the questions written in his eyes. John may want answers but Oliver was in no mood to answer them. 

"She's been removed. Are we putting the usual tail on her?" John’s tone is gruff and wary as if he already knows that Oliver won’t be working as per usual. 

"No. She won't be a problem."

"Since when are you so quick to trust a pretty face?"

"We're old..." Oliver pauses as he struggled to find the right label to describe what Felicity Smoak means to him, "friends. I guess." 

John crossed his arms and leaned against the wall with a raised eyebrow, "So you slept with her."

Oliver lets out an exasperated, "Diggle" and wiped a hand over his face. 

Oliver can see the curiosity growing on John’s face, that damn, unrelenting eyebrow still perfectly posed. At times like this Oliver wondered if it was his eyebrow that was the most toned muscle in John Diggle’s body as opposed to the tree trunks he called arms. “You slept with her more than once.”

Oliver debated just coming out with the truth just to shut his friend up but even after all these years he still wasn't comfortable talking about it, wasn’t comfortable talking about her. Instead, Oliver looked to the ceiling waiting until John figured it out on his own.

Oliver starts to slowly count the seconds that tick by as he waits for John to connect the dots. He hears John cross his office and settle in the same chair Felicity occupied minutes earlier. Oliver just counts to eighteen when he hears John’s soft response as if speaking it would make it so, "Don't tell me that was her." 

Oliver looked back at him with a sardonic face, "Okay, Dig, I'll tell you it wasn't her." 

"Shit."

Oliver let out a breathy chuckle and scrubbed his face with both his hands. 

"She's the reason you're here. The reason you..."

"Stopped shooting bad guys?" Oliver interrupted. 

John's eyebrow jumped back up in full force and Oliver chuckled looking a marginally lighter, "Okay, so... worse guys? Or do you prefer enemies of Bratva?" giving his best impression of Anatoly.

Oliver can feel the tension fluctuate in the room. He’s not sure what he feels in this moment but he knows he doesn’t want John pitying him. Maybe, just maybe if he makes jokes John won’t see how twisted up his gut is by seeing Felicity again, "So what are you going to do about it?" 

By now Oliver should know better than try to hide his feelings from his friend but also knows this is a pandora’s box he’s not ready to open. Just the idea of following up on Felicity brings the tension back into his body, his shoulders knotting up and a pressure building behind his eyes. He doesn’t mean to make his voice sounds so cold and distant when he replies, "Nothing."

\---------------------------------------------------------------------------------------------------------------------------

Felicity looked in the rearview mirror as she pulled away from the casino and speeds down the street until she sees an unmarked alley. She shifts the car into park before she has a panic attack. Her breathing is labored and her mind is fogging up and she loses focus on what the rest of her body is doing. It takes her a good ten minutes until she is able to think about anything other than those cold blue eyes. 

Felicity inhaled a big breath through her nose and slowly breathes it out her mouth, "Okay. So you just saw Oliver. For the first time in five years, you saw the love of your life." Felicity furrowed her brow, "Love of your life? Really? Realistically speaking, there can be more than one love of your life." Felicity rolls her eyes, "That is if you opened yourself up and didn't dwell on the past and actually had time between work, and helping your mother, and..." Felicity pressed her lips together and closed her eyes attempting to win back her focus. "You just saw Oliver. Who you love. Loved! Past tense. Definitely past tense, because you shouldn't love someone who very recently vaguely threatened to kill you or cut off your hand or whatever those mob guys do for punishment nowadays." Felicity pauses and takes a few more deep breaths trying to slow down her breathing and her mind. "But the key word there is shouldn't," Felicity mumbled. She closes her eyes and starts to slowly beat her head against the headrest. 

Felicity takes in another deep breath and pulls her car into reverse out of the alley and heads towards home, "Frack. Frackity, frack, frack." It's still early on in the evening and her mother wasn't expecting her until the wee hours of the morning so Felicity takes the long way home. "God he still looks good." She snorts, "Of course he looks good, can't fall out of shape when you're the best assassin for the Bratva." As Felicity turns on the street towards her home the houses start to blur together and she feels an ache deep within her chest and the tears slowly start to trickle down her face. As she pulls herself into her garage she checks the clock. It's only a few minutes past eleven and since her original plan fell through she just stays in the car and allows herself to cry for five minutes before she has to go back to her world of stress and responsibility. 

Once her time is up and she's fairly certain the tear tracks and red eyes are under control she heads into the house but pauses when she hears a Spice Girls song playing at a fairly decent level and two voices singing incredibly off-pitch. Felicity takes one last deep breath to center herself before she enters but she can't help the twitch of her lips into a smile. 

As she stealthily entered the living room she sees her mother, Donna, with her hair pulled up into four ponytails along with at least fifteen butterfly clips moving jerkily to the music. Felicity thought she could see glitter in her daughter, Maisy’s, hair. It is done just as outrageously as Donna’s but she sports blue eyeshadow and bright pink lips and is jumping up and down on the couch using a hairbrush as a microphone as she attempts to spit out the lyrics to "Wannabe" as best as a four and a quarter-year-old can. Felicity quickly pulls out her phone and takes a video of the rest of the song purely for posterity and not future blackmail. As the song ends and the next comes on Felicity switches to the app on her phone that controls 95 percent of the technology in her house and turns off the music. Two blonde heads snapped up to look over to her, her mother looks sheepish, while her daughter's eyes have doubled in size terrified of what the punishment will be for staying up past her bedtime. 

"Maisy Olivia Smoak what are you still doing up?" Felicity asks in a tone that is simultaneously stern and loving.

"Nana and I were going on a world tour!" 

"Oh? And what fabulous country were you just singing in?" Felicity walked over to the couch and gathered her daughter in her arms as she starts heading to the bathroom.

"Paris!"

Felicity smiles, "The country you were in is France; Paris is the city." Felicity corrected gently, "It sounds fabulous. Were the tickets sold out?" Felicity sets her daughter on the counter next to the sink and gets out the makeup removers and starts wiping her daughter's face but not before her daughter can send out a scolding look. 

"Duh, mom." 

Felicity laughs as she starts to pull accessories out of her hair, "Well that's good. I'm glad you had a good time with Nana but now it is definitely time for bed." Felicity handed off her toothbrush before turning around and finding Donna already standing there holding a pair of Princess Sofia pajamas. 

All dressed and ready for bed, Felicity tucked Maisy in and laid next to her on top of the covers and grabbed some of their favorite books that are stacked right next to the bed, "What story do you want tonight sweetie?"

"I don't want a book tonight mommy," Maisy yawned widely and sunk lower under the covers, "tell me about the Green Arrow and the IT girl." 

Felicity froze in the bed and looked down at her daughter who is very nearly asleep and sighed, "Not tonight sweetheart, another time I promise." Felicity slowly got out of bed and kisses her already sleeping daughter on the forehead and sneaks out of the room.

Donna is leaning outside the door sans crazy hair, "I didn't think you would be back this early." It's a question and a concern all wrapped into one. 

"I got caught at the first casino I was at before I made it out the door." 

Donna's reaction is as Felicity expected with a loud gasp and an equally loud, "WHA-" before Felicity slaps her hand over her mother’s mouth and drags her off to the kitchen. Setting Donna down at the kitchen table and finally removing her hand from her mother's mouth, "It turned out okay because I actually knew the owner of the club and he let me off with half my earnings as long as I agreed not to return."

Donna's eyes narrowed and there's an edge to her voice that is very seldom there, "You're telling me that you got caught in some mob casino? You could’ve been killed! Or worse!”

Felicity's head tilted to the side, "What's worse than death?"

Felicity has rarely seen Donna this angry as she watches let out a huff of anger and is shaking her pointer finger in Felicity’s direction, "That is SO not the point Felicity Meghan Smoak!" Donna takes a step closer, looking to Felicity like she is ready to hit her stride in scolding, instead Donna pauses and tilts her head to the side, "Have you been crying?" 

Felicity is sick of being on edge and though her relationship with her mother is touch and go she feels like she doesn't have an out and is too tired to look for one, "Yes."

Donna just stares at her for a long minute and the realization slowly hits, "It was him, wasn't it? He owns a fucking casino." Donna's eyes get big and she claps her hands together quickly in excitement, "Get him to give you the money! He's got to be loaded!" 

Felicity shakes her head and answers tiredly, "No mom," and walked towards the kitchen’s exit ready to head to bed.

"Just think about it! It's the perfect solution!"

Felicity turned to her mother at the threshold, "No. It is definitely not the perfect solution. End of story. Goodnight."


	4. Chapter 4

**Notes for the Chapter:**

> Thanks for reading!

Felicity had been fidgeting the whole ride home with her mother after her second encounter with the super hot stranger. Oliver, he has a name, she thought. A good name. A name that possibly made him even hotter. She's fidgeting because she's not sure what to do, whether she should go back to the bar or just hide in her mother's apartment. Felicity does know that if she does show up to the bar again she's pretty sure she's going to jump him. 

He had made it abundantly clear that he's interested in her and it has been awhile since she got any. She tapped her finger on her thigh as she did the math; it has been around fourteen months since her relationship with Cooper imploded. Fourteen months of self-imposed climaxes. 

It's not like there haven't been opportunities for one night stands since Cooper but Felicity had never really understood the whole hookup thing. She either gets too emotionally involved or scares them away with her incessant babbling before the deed can be done. But Oliver doesn’t seem to be scared away by her babbling and promised to be there tomorrow with his penis ready and willing and she thinks that maybe she'll be willing as well. Maybe. 

Once they're home in the kitchen, Felicity and her mother start gathering supplies for supper. If they work together in the kitchen supervising each other they tend to only get food poisoning once a year. While she’s chopping a green pepper, Felicity can feel Donna’s eyes glancing over at her periodically, "Alright baby girl, what is your deal. You haven't spoken a word since I got off my shift. Instead of talking my ear off you can't seem to stop fidgeting. What is going on?" There is definitely concern in her voice and even some annoyance because Felicity knows she hasn’t quit fiddling since she got in the car and she knows how much her tinkering can drive her mother crazy.

Felicity shifts uncomfortably, "I don't know if we can talk about this." Felicity loves her mother but 7 out of 10 times they are not on the same wavelength and that frequently causes a lot of tension in the house. On the other hand, Felicity knows that her mom knows a bit about the subject she's been chewing over since Oliver left her squirming in her chair. Until her mom finally got off her shift, Felicity was seriously debating the pros and cons of masturbating in the casino bathroom. 

"Felicity, baby, you know you can talk to me about anything." Felicity nods, debating whether she wants to talk about casual sex with her mother while also thinking of the other people she might have this conversation with. She's pretty sure none of her MIT friends will be able to reconcile the Felicity they know from school who wants real relationships and was still fairly broken hearted over Cooper with the Vegas Felicity who wants to use a man's extremely hot body for her own personal gratification and never look back. 

Her mouth decides for her as she hears the words, "How does casual sex work?"

Her mother stops cutting up the pepper and gives Felicity a slightly dumbfounded look. Felicity can feel the momentum building and knows this isn’t a conversation she actually wants to have with her mother, she can’t even meet her mother's eyes as she mumbles, "Sorry this was a bad idea, forget I said it."

Felicity can barely believe it’s her mother speaking when she hears the words, "What do you mean how does it work?" It sounds clinical and detached, words she would never use normally when she was talking about her mother and sex. Thank god those topics didn’t compound frequently. 

Felicity still can’t seem to meet her mother's eyes as she mutters, "I don't know. I've never done it before. It's never really, uh, panned out, so to speak." Felicity can feel the blush burn up her neck and on her cheeks and wonders if she has ever felt so embarrassed in her life. 

"Well, drinking helps, but not so that you can't give proper consent but enough to loosen you up a little bit. Calm your nerves. Find a guy, who's nice and respectful, who'll buy you a drink without automatically expecting you to blow him." 

Felicity's eyes finally snap up, "MOM!" 

"What? You wanted to know and I'm not editing it to fit your delicate nature."

Felicity groans, "Mother, I am not delicate. I just like being in a relationship for sex."

"Which is noble," Donna quickly adds, "Let him take you home or back to his hotel room and let your bodies do the talking if you know what I mean." Donna pauses like she is waiting for confirmation before she continues.

Felicity eventually grounds out, "Yes, mother, I know what you mean."

"Always go back to his place, fewer strings if he doesn't know where you live or gets too clingy and wants to stick around. Set the terms before hand, let him know that all you're looking for is one night that's it." Donna taps a finger to her chin, "Double up on protection, even if he doesn't want to, insist. Then bing, bang, boom put your clothes on and leave or grab your phone set the alarm to vibrate under your pillow to wake you up before he does." 

Felicity nods her head as she listens to what her mother has to say. Donna gives her another skeptical look and Felicity knows she’s not going to like the next question, "So who's the guy?"

Felicity looks up confused and only slightly terrified because her mother works all the way on the other side of the casino and doesn't give Rich, the new bartender, the time of day so she can't know about Oliver, "What? Um, what guy?" 

"I may not be some MIT genius like you but my daughter just asked me about casual sex she either has a guy in mind or she's turning into a boy scout trying to 'always be prepared.'"

Felicity slowly starts backing out of the kitchen, "Boy Scouts. Definitely boy scouts. You know me always planning ahead. Speaking of ahead I've got some things to look up for classes this fall." She stumbles a little before turning around and heading out the door before stopping again and looking at her mom, "Uh, thanks. What you said was helpful and didn't scar me for life. So, thanks."

"Anytime baby girl, now if you want any pointers on positions-"

"MOM! We just found the line. No more talking. I'm to my room, call me when dinner’s ready."

 

\------------------------------------------------------------------------------------------------------------------------

 

Oliver slowly opens the door to the foyer of his childhood home hoping not to wake the two potential inhabitants in the house at the ungodly hour in the morning. Before he turns to shut the door he sees his sister slowly sneaking up the stairs. 

"Speedy." Oliver calls out in a stage whisper, the third inhabitant was probably not home anyways, "You just getting in?" 

Oliver's sister spins on the stairs to face him, her bobbed hair spinning straight out behind before settling back down looking like she hadn't had a twelve hour day but rather just left the salon. When she spots her brother slowly making his way up the stairs she rolls her eyes. 

"Ollie, I own a club. We close really early in the morning. I'm a responsible business owner not some teenager coming home from a bender."

"Thea," Oliver rubs a hand over his face taking a position opposite her on the top of the stairs far too exhausted to get into an argument with his sister, "that's not what I meant. I'm not trying to be suspicious. Supportive, actually. Concerned even."

Thea's features all scrunch together, "I know, I'm sorry. It's just, I know what it’s like being the screw-up," Oliver snorts and Thea cracks a smile "Okay, so I was never as bad as you, but this is real Ollie, no favors are being cashed in or back alley deals. I’m not going to screw this up." 

Oliver crosses his arms and leans against the banister opposite Thea. She looks older than she did even this morning when he saw her over breakfast, barely above a whisper he states, "I'm proud of you, Thea." 

"Wow, that almost sounded sincere." 

Oliver rolls his eyes at her antics. It’s not often that he voices his feelings even to those he loves most, "I am proud of you," stating it louder and much more convincing. 

A shy smile sprouts over Thea's face before turning full blown and radiant, "Why thank you brother dear, having the only Bratva free business in the family is pretty great."

Oliver pushes himself off the banister and nods his head down the hallway off to the bedrooms waiting for Thea to follow him. "It's not totally Bratva free..." 

"Whatever, Ollie, once I pay off the loan you still only own ten percent but you don't own it as Bratva Captain, Oliver Queen. You'll own it as my stupid, masochistic robot brother who sucks at giving compliments but is willing to ask about my day, even at," Thea looks down at her watch and wrinkles her nose, "four in the morning even though he looks like complete shit." 

A ghost of a grin crosses Oliver's face and since they've reached Thea's bedroom door, Oliver leans over and kisses Thea's temple mumbling a good night into her hair and continues down the hall to his room. 

"Ollie." Thea's voice is hesitant and when Oliver turns he sees her rocking up in down on her toes, her most obvious nervous tell. 

"Yeah, Speedy?" Oliver's hand on his doorknob, he can practically hear his bed calling out to him. 

"Um..." Thea tucks her hair behind both ears and continues rocking looking everywhere but at his face, "You, uh, look like shit and I was wondering why you look like shit." It all comes out in a rush and Oliver tries not to tense too much at the accusation but he promised not to lie to her anymore so he remains silent. "You didn't, uh, fall off the wagon or something, right? I mean, I see that look in your eye and it reminds me of." Thea cuts herself off and there is a tense silence between the two siblings. "Back then."

"Thea, look at me please." Her eyes slowly make their way back to his face, "I didn't kill anyone. It was just a bad night at the casino. I'll see you at breakfast." His attempt at a smile makes Thea grimace but it seems like she believes him. 

"Okay, tell me at breakfast?" She asks timidly, which is strange for Thea.

A long breath exits through Oliver's nose as he stares at his hand on the doorknob. "Maybe." Because he's not sure he can talk about it but he's trying not to shut her out completely. "At brunch. Breakfast is going to come too fucking early." 

He hears Thea laugh before bidding him goodnight and entering her room. He waits to enter his until ten seconds after he hears her door click shut, a habit he picked up when they were younger just in case she found monsters under her bed. 

When Oliver enters his room he strips his clothes on the way to the en-suite bathroom and turns on the shower as hot as it will go, hoping the current burning sensation on his skin will distract him from the memories of being burned by Felicity Smoak. It doesn't help one bit.

**Notes for the Chapter:**

> All publicly recognizable characters, settings, etc. are the property of their respective owners. The original characters and plot are the property of the author of this story. The author is in no way associated with the owners, creators, or producers of any previously copyrighted material. No copyright infringement is intended.


	5. Chapter 5

**Notes for the Chapter:**

> Thanks for reading! Sexy times at the end of this chapter.

Oliver's stress levels were higher than he expected when he walked into the Pink Flamingo the next day. The mission was not going well and the men he was working with were practically incompetent. Oliver needed to put those thoughts away even though the stitches on his right side were making it harder to focus on how he would be getting Felicity back to the apartment he is staying at. Hopefully, she’ll be eager enough to fuck before all his clothes can hit the floor. The fewer the questions the better for both of them. 

He sees Felicity before he even realizes he's looking for her and his eyes widen in surprise at what she's wearing. He can't help the tilt of his head to the side as he walked down the stairs and crossed the room towards her. 

Her makeup is a little darker than the last two days and her hair is in soft waves down her back, the usual ponytail is nowhere to be seen. It's the dress that has his mouth going a little dry and his dark wash jeans stirring. It's black and mostly backless with only a couple of thick bands the run across her mid back and her shoulders. Oliver smiled wider when he realize she wore it for him. 

Confident, Oliver walked over and sat next to her signaling to the bartender, it's the same one as yesterday and he's openly staring at Felicity. Oliver can't really blame him. 

"Vodka, neat and a Shirley Temple please."

Turning to face at Felicity he sees her fiddling with the hem of her dress and avoiding looking in his general direction. 

"Hello, Felicity. You look lovely." 

The bartender set their drinks in front of them. He sees Felicity take a deep breath and look at him. Before he can even reach for his glass she takes his vodka and downs it in one gulp. Oliver smiled at the slight face as she shakes her shoulders forcing the drink down.

She finally spoke with determination, "Okay let's do this."

A shit eating grin exploded over Oliver's face but he can’t help but play coy, "Do what?"

Felicity made a disgruntled noise and looks away and mumbles, "Don't make me say it."

The grin on Oliver's face slowly slipped but his eyes are on her as intently as ever. "Felicity, we're not doing anything unless you can tell me what you want. You're running this show. I will not force you to do anything you don't want to do." 

She looked him in the eye, "Can I trust you? I know you've been laying your slick moves on me but I still feel like I can trust you." She tilted her head to the side, "Why is that?"

The slick grin returned reappears on Oliver's lips, "I guess I just have one of those faces." As soon as the words slipped out of his mouth he sees Felicity’s nerves kick up and start to shut down. Oliver decides to drop a small portion of the mask he hides behind when he's out in public partly because he wants to get laid and partly because this woman in front of him intrigues the hell out of him. "You can trust me, Felicity. If you want me to leave right now and never bother you again I will. If you want to have sex with me back at my apartment I would be more than happy to oblige." Oliver felt the childish urge to cross his fingers. 

Swallowing a big breath of air Felicity looked to him and slid off her stool, "The sex thing. Let's go do the sex." Oliver's grin appeared back on his face it feels foreign after years of disuse. "I mean, let's go. Back to your place. To have sex." She closed her eyes and pressed her lips together. "Am I ruining this?" 

Oliver chortled and cupped her face in his hands, her eyes flashed open and he slowly leaned into her waiting for her to object but she shows no sign of wanting him to stop so he closed the distance. Their lips met tentatively and there's some small spark that Oliver quickly ignored. He takes in the softness of her lips and the way she tastes like cherries and vodka. He slowly licks her lips trying to open her up and deepen the kiss but he feels her stiffen so he stopped and leaned back still keeping his hands on her. "Not here!" Oliver looked at her and let out a full jovial laugh and he refused to think about the last time he laughed so freely. 

"Alright Felicity, not here." Oliver still chortling, slid off his stool and grabbed her hand and leads her to his BMW. Oliver speeds all the way to his apartment alternating between shifting gears tracing patterns into Felicity's exposed thigh. As soon as he gets her out of the car he's touching the exposed skin on her back and guiding her to his apartment kissing along her neck. At his door, he takes one free hand and grabs for his keys while the other slides to her side his thumb finding its way under one of the connecting panels of the dress skimming the side of her breast and he feels her shiver. Oliver smiled, loving how responsive she was and they had barely even started. Finally, he got the door open and they're inside and he's already pressing her against the door his growing erection is settled nicely between her thighs and he is attacking her mouth with desperate kisses teeth and tongue dancing against each other. Oliver can’t stop his mouth from moving down her throat pressing sloppy kisses down every inch. He has never felt this desperate need to consume her and be consumed in return. 

Just as quickly as things had started Felicity's breathing changed suddenly growing faster and instead of pulling him closer her she was pushing him away. 

"Stop." Felicity’s eyes were wild as she gulped in air. "Can't do." Gulp. "This." Gulp, gulp. "Too busy." Gulp. "Panicking."

Oliver had seen his fair share of panic attacks but he'd never seen one from a woman he's about to have sex with. "Felicity look at me.” Her eyes are slightly glassy and she’s not focussing on his face so he pulls her hands up to his chest, “Breath with me. When I breathe in you breathe in. When I breathe out you breathe out. Okay?" 

He doesn’t wait for a response as he started his breathing, his chest visibly rising when he breathes in her hands still on his chest. It takes a few minutes before she's calmed down. Her eyes are focused on his and the words that have been building up in her mind tumble out when she's regained the proper use of her lungs, "I'm so sorry, Oliver. I just never do this. And by this I mean sex. Well, I've done sex. Only a few times but I was good, well I don't know if I was good good or just good enough to. You know what? So not the point, I mean I've never done this. This as in the one night stand thing we're doing, if we're still doing it since you know I had a panic attack and can't stop talking. Stop talking now. Right now." 

There's a long drawn out silence where Oliver can’t help but stare at her trying to understand all the words that have been poured out at him while also taking in the magnificent blush that has spread all over her face and trickled down her neck. 

Felicity started to slide out from against the wall, "I'm just gonna, um, go. Catch a cab or something less humiliating." 

That shakes Oliver back to life and he put his hand on her hip keeping her against the wall but loose enough that she can easily slip away from him if she chooses. "Felicity." He tilts her chin so she is once again looking at him there are tears in her eyes and he's not sure whether they're from the panic attack or the embarrassment or both. "If you still want to do this I'm in but we'll take it a little slower." 

Confusion colored her face, "Really. You're still in? Why?"

Oliver slowly leaned in and started peppering kisses down her neck, "Because you're beautiful." Kiss. "Because you're intelligent." Kiss. "Because you're incredibly responsive." A kiss from him and a shiver from her and Oliver can’t keep the smile off his face as he continues his trek, "Because I would really like to let off some steam by fucking you until you can't remember how to use your legs." Oliver ran his tongue from the bottom of the V in her dress up her cleavage to her collarbone giving it a light bite. He wanted to add that she makes him smile, hell, he’s even laughed more tonight than he has in the last four years but he knows that would be far too intimate for a random fuck. Especially since when he thinks those things he wants to have a panic attack. So he stops talking and hopes his actions are speaking for him pulling back and seeing the lust back in her eyes, the panic completely gone. 

"I want this. Really, really bad. But I'm nervous. Ergo the whole panic attack thing. But slow. Slow would be good."

Oliver drops to his knees in front of her and starts massaging her thighs and alternating kisses between her two thighs slowly moving up to her core where Oliver can smell her arousal. 

Felicity's voice is shaky and he’s certain that it’s from arousal and not fear, as she tries to figure out what he's doing. "I thought you said, oh" she jumps as he slid her dress up over her hips her lace thong exposed, his thumb briefly brush across her slit. "Slow. You said slow." 

Oliver sees Felicity twisting her hips trying to create more friction, anything other than the soft kisses and the slow touches from his ever moving fingers. "Felicity, I have a lot of built up energy. I could do this," his tongue slides slowly over her wet underwear, "all night," he says keeping his mouth close to her center breathing heavily. 

Felicity's eyes are closed and her head lightly bangs against the wall, "Holy shit." A wry smile appears on her face and Oliver is glad to see that his feisty girl is back, "Does all night oral include breakfast?" 

With one hand he pulls her thong off to the side and with the other, he casually runs his finger up in down her slit in time with the clock he hears ticking in the kitchen. Every time his finger brushes her clit she trembles. Oliver gets a hold of her thigh with mouth and bites and suck until he's sure there will be a bruise in the morning before replying, "Yeah, Felicity, I'll make you breakfast."

"Make me breakfast?" Her voice is airy and he can tell she's struggling to focus, "You more of an omelet guy or a pancake guy? Because you seem more like a panc-aaccck!" Oliver's mouth descends upon her soaking slit, flattening his tongue on her engorged clit lapping up her juices. 

There's another smile on his face when he replies, "Let's wait to think about breakfast until the morning." And goes back to sucking on her clit, shoving one of his fingers up her pussy. Breakfast was going to have to wait.

**Notes for the Chapter:**

> All publicly recognizable characters, settings, etc. are the property of their respective owners. The original characters and plot are the property of the author of this story. The author is in no way associated with the owners, creators, or producers of any previously copyrighted material. No copyright infringement is intended.


	6. Chapter 6

**Notes for the Chapter:**

> Sorry for the delay! My Ao3 was being a finicky little goober.

Felicity woke with a start, slightly disoriented; her heart was racing, and she could feel a distinct moisture between her thighs. Felicity felt slightly disoriented wanting to hold on to the memories of her dream and lock them away all at the same time. The flashes of her first night with Oliver make her want to slide her hand down her stomach and take some of the edge away but after seeing Oliver in the flesh rattles her more than she would like to admit and knows she won’t come to completion before her mind takes her down an Oliver spiral. 

Once her breathing is back under control she goes to take a cold shower. It’s 4:38 in the morning and on any other day she wouldn’t get out of bed before at least the promise of two cups of coffee and poppy seed french toast but she knows she won’t fall asleep again. Being awake also means that she can fight off thoughts of Oliver better than her apparently unreliable subconscious. 

After her shower, Felicity heads to the kitchen with her tablet so she can start on her daily coffee allowance, today she already knows she will reach her self-imposed maximum of ten cups.

Once she finally has her favorite mug filled up to the brim, a Mother's Day gift from her daughter last year, she fires up her tablet and looks at her family's financial situation. With her student loans still piled up, along with Maisy's hospital bills from when she had pneumonia last year, and her mother's online shopping addiction, they're always pinching pennies in the Smoak household. It's one of the many reasons they packed all their things and moved to Starling City three months ago. Felicity is doing whatever she can to keep them above water but they’re barely treading as it is. 

When Felicity found out about her mother's erroneous amount of debt she was furious, chopping up all of Donna’s credit cards in a grand fury, making hard plastic confetti. Felicity already had one life to take care of she didn't know if she could or should handle another one. It felt like she had just gotten one out of diapers when she discovered the other one binge watching QVC and finding strange packages showing up at their apartment door. It wasn’t until Jerry, from her mom’s work, had caught up with her asking about a loan repayment schedule that Felicity really got worried. 

They needed a change, desperately, so when she was hired by Palmer Technologies in Starling City she leaped at the opportunity. She may be a lowly IT gremlin but she knows there will be opportunities to move up in the corporate hierarchy. 

So far, their new life in Starling had been perfect, she finally felt like where she was supposed to be in life until last night. She still couldn't believe her luck. She knew she could figure out the odds of running into the one person she was running from but that meant opening the box and she kept under lock and key, except when she was dreaming about what his tongue could do between her thighs. 

She went to her purse and grabbed the envelope Oliver had handed her last night; it would definitely help with some of the payments she needs to make but it won’t cover for very long. Felicity debates whether she needs to pick up more freelance work. It would be a hell of a lot less risky than counting cards in mob casinos but the pay isn't as good. 

"Mommy?" 

Felicity turns to see her little girl, barely cognizant, shuffling over to her. Felicity looks to the clock. She's been so lost in thought that she has barely noticed the hour that has gone by but it's still early for her little one to be up especially after such a late night.

"Good morning my sweet baby, what are you doing up so early?" She lifts Maisy into her arms and they head over to the couch for some cuddle time before Felicity has to get ready for work.

"Bad dweam," Maisy replies rubbing her eyes and tucking her head under Felicity's chin.

"Do you want to talk about it?" Felicity is fairly certain she knows what the answer will be even before she feels her daughter shake her head no, her daughter often keeps things close to the chest and Felicity has learned not to push the girl too far or she will completely shut down and not talk to anyone for the next two hours at least. So instead they sit in silence and Felicity pretends to be patient while her daughter decides whether to put a voice to her fears or not. 

The silence is not uncomfortable and Felicity is almost certain her daughter has fallen back asleep until she hears her daughter mumble into her collarbone, "Where's my daddy?"

Felicity feels herself go still and tries to figure out a way not to lie to her daughter, "Why do you ask my sweet? Is that what your dream was about?"

Maisy nods into her shoulder, "Does he not love me?" 

Felicity is sure she can feel a dampness on her shoulder and she feels her heart breaking for her daughter. She tries not to indulge the grief that she feels tapping on her shoulder, attempting to push it away before it joins the rest of the guilt she feels for making the decisions she felt had to be made to make a better life for her daughter. But now she's facing a question she doesn't know the answer to and she hates lying any more than she absolutely has to, "Oh my sweet baby," and it's as she's whispering into her daughter's ear she realizes that she has joined her daughter in tears, "I'm sure your daddy would have loved you very much. You're impossible not to love!"

"Then why isn't he here?" Maisy sniffles a bit before giving up and wiping snot on her sleeve. Felicity recoils a bit at her daughter's manners but decides now isn't time for an etiquette lesson. 

Felicity sighs again, she did not have enough sleep to deal with this type of interrogation from her four and a half-year-old. She knew these questions would be coming she just didn't think that they would be happening now, not right after she saw Oliver. She wished she could tell her daughter the whole sordid tale but her life has never been fairytale perfect. Felicity frowns, unless she counts Grimm's tale or German nursery lessons, which are getting more fitting all the time. Instead of getting her digits removed for sucking her thumb she nearly got her digits for counting cards but she needs to stop her internal dialogue because her very impressionable daughter is looking up at her with her beautiful, big blue eyes waiting for an answer. An answer that Felicity didn't want to give, because how do you tell your daughter her father doesn't even know she exists.

“Sweetheart. Sometimes daddies aren’t around and that hurts because every little girl and boy want their dad but sometimes” Felicity scrambles for something that will make sense to her daughter, “...hmmm...Remember last Halloween when you ate half of your candy in less than an hour?”

At some point during either the internal dialogue of frightening fairy tales or fumbling for an answer Felicity has leaned her head back against the couch and closed her eyes so once again she feels, more than sees her morose daughter’s answer so she continues her previous thought, “Remember how you felt?” 

“My puke was brown.” Felicity can’t stop the snort and lifts her head to look at her daughter. 

“Yes, my beautiful girl, it was and all over you and your bed too. But that wasn’t quite the point of my story, sometimes we make choices and we have to deal with the consequences.”

“Con-swe-kenses?”

“Yeah.” Felicity pauses, trying to come up with a way to explain it to her young daughter, “When I found out you were in my tummy I was so scared. I ran from your daddy and now you have to deal with not having a daddy because I was scared.”

Felicity looked down at her daughter’s face hoping she won’t see resentment or anger but knowing the little girl had every right for whatever emotion she chose. Maisy has a furrowed brow and a little frown while deciding her mother’s fate. Felicity bites on her lips to hold in her smile because she often wonders whether her daughter got any of her genes or if Maisy is 100% her father. But Felicity can only allow a few more moments of her daughter’s introspection before she has to know what is going on in her mind, “What are you thinking sweetheart?”

With a heavy sigh, she responds, “Lots of things mommy. I want a daddy. My friends all have one and they seem nice.” She makes a grunt and her nose is crinkled and Felicity knows she has come to her final decision and she won’t change her mind (Felicity can never decide if this stubborn trait comes from her or Maisy’s father or both which terrifies her). “I just have to be brave.”

Her response throws Felicity for a loop but she feels emotion building up in her gut. 

Maisy rolls her eyes like the answer is obvious, “You were scared so I don’t get a daddy and that’s bad. So maybe if I’m brave, you don’t have to be scared anymore and I can get a daddy.”

Felicity wants to object and tell her that’s not quite how it works when her mother joins them in the living room her eyes’ sparkling a bit and Felicity knows that she has been eavesdropping again. Maisy scrambles out of her lap and Donna takes over Maisy’s morning routine allowing Felicity time to finish getting ready and head to work. She takes a deep breath as she starts her car hoping one that one day she’ll be as brave as her daughter.

**Notes for the Chapter:**

> All publicly recognizable characters, settings, etc. are the property of their respective owners. The original characters and plot are the property of the author of this story. The author is in no way associated with the owners, creators, or producers of any previously copyrighted material. No copyright infringement is intended.


	7. Chapter 7

**Notes for the Chapter:**

> Thanks for your patience. Enjoy!

Felicity wakes slowly stretching, taking up the entire bed as she does so and burrows back down under the soft sheets that smell clean while also getting something that is all man. It’s then that bolts up and goosebumps race to cover her skin and she takes in the room. She doesn’t remember much of it from the night before. It’s clean and rather sterile and reminds her of any upscale hotel room. There is nothing in this room that is personal, no pictures, just some abstract art that looks cheap and expensive at the same time. She doesn’t even see any clothes on the floor and that is when she realized that she’s stark naked and none of her clothes made it to bedroom from the night before. 

Felicity contemplated running out to the hall to gather her clothes but the bathroom is calling her name and Oliver might be out there and she’s not sure she’s not sure if she is brave enough to see him yet. She looks to the alarm clock near the bed noting that at least it is still morning. 

As she entered the bathroom she saw the dress and her undergarments hanging on a hook under plastic. She can’t help but snort, this is the first time her underwear has ever been dry cleaned. Hell, if money is short at MIT, which it usually is, she just flipped her underwear inside out so she can hold off doing laundry until she has enough quarters but that is a secret she is keeping to her grave. Except now her bra and her underwear each have a separate hanger and she feels mildly embarrassed to have had strangers cleaning and pressing her panties. Felicity can’t help but think she hit the big time when she fell into bed with Oliver. Upon first meeting him she was sure that he would kick her out of his bed after he reached climax but instead he’d taking exceptional care of her undergarments. 

Felicity can’t help but think that she should have left earlier. Her mother told her that this was not how one night stands were supposed to go and Felicity is not in a place for commitment or secondsies. But she felt so refreshed and content and her brain isn’t moving as fast it usually did when she wakes up. And there was just something about the way Oliver treated her last night that makes her think this morning after “thing” that’s about to happen is going may not be as awkward as it could be, though knowing her own ability to turn a phrase it could get very awkward very fast. 

On the table next to her clean clothes is a towel and all the amenities needed to take a shower in the same size containers that motels provide. Felicity wondered if Oliver was this hospitable to all his sexcapades. If this is how all her one night stands will go she could easily make this a habit of hers, but she highly doubts that she would get this treatment from falling into bed with just anyone. Oliver is special. Felicity froze at the notion, her hand outstretched checking the water temperature. That line of thinking will lead her nowhere good. This was a one-night thing; she’ll shower and leave hopefully without seeing Oliver. Maybe he’s already at work, on a Saturday morning, or out finding his next conquest. As she showered she can’t help but think up possible excuses for why Oliver won’t be out there when she gets out each becoming more implausible. 

Felicity tentatively stepped out of the bedroom and was immediately assaulted with the scent of fresh baked bread, her stomach growled at her like she hadn’t fed herself in days. She entered the kitchen expecting, well she’s not sure what she had expected but it definitely wasn’t Oliver bending over and taking something out of the oven. Her inner dialogue goes silent as she thought of all the things she’d like to do to that ass. She was so lost in thought, beautiful explicit thought she jumped when Oliver called her name with the proper morning greeting.

Felicity responded before thinking which unfortunately is her default setting more often than she would like to admit, “Sorry, I was staring at your ass.” 

Felicity closed her eyes her mind finally catching up with her mouth. She should have never opened her mouth before coffee. Her thoughts are once more interrupted but this time by Oliver’s breathy chuckle. She attempted to correct herself, “I mean, good morning. Nothing about your gorgeous backside.” She froze clenching her jaw and changed the subject entirely trying to move past her embarrassment, “Whatcha cooking?” And Felicity literally bit her tongue to stop her from tacking on the ‘good looking.’

There’s a small grin on his face, “Banana bread,” is his simple reply gracefully ignoring her remarks about his ass; she can’t help but feel grateful for that. 

A mirroring smile grew on her face and suddenly she felt shy. After everything that happened last night and the dry cleaning this morning she doesn’t want to push him past the limits of his hospitality and invite herself to the food he’d made, though he did say something about breakfast at one point last night but holding him to his mid-coitus promises seemed petulant. 

As if he was reading her mind, “So I know last night I promised pancakes but I had some bananas that were going bad and uh,” he looked away from her and Felicity can only describe him as adorable as he started to shuffle his feet, “I was thinking banana bread French toast. Is that okay? If you want to stay? Or I can call you a cab if you needed to head out.” 

He’s giving her a free out. Felicity knew this and shouldn’t even be thinking of staying. She wasn’t going to make this a habit, especially with Oliver. On the other hand, it’s a Saturday and she has nothing to do today. Her stomach growled and Oliver looked so cute and insecure. While Felicity knew that he was giving her an out he was also opening a door, that whatever happened last night could happen again. Maybe they could become friends with benefits when they’re in the same timezone. The food is enough to tempt her but the idea of continuing the amazing orgasms and comfort he was able to provide for her last night when she was panicking, that she is enough to see where it goes but then again this could all be in her head and all he wanted to do was feed her and then kick her to the curb. 

“So is this a normal morning ritual for your nightly conquests?” Felicity made herself comfortable on a stool watching as Oliver continued to prepare breakfast. Watching him work in the light of day fascinated her because there is a stiffness to his movements though still incredibly fluid.

He shifted on his feet and beats the eggs a little faster, “Uh, no.” Felicity stared at him hoping that he will open up a little bit more but she’s getting the impression that Oliver is incredibly cagey with information. It seems like he would rather get a root canal than give up his favorite color or shoe size willingly. Just when Felicity started to think of some other topic that will get this pacing panther to calm down he spoke again, “I usually don’t bring back women to my place at all.” Felicity scrunched her nose trying to read between the lines but comes up blank. “You seemed different.” 

Felicity shook her head to try to get past her confusion. She may be a genius but her interpersonal skills have always fallen a little bit flat and Oliver is an enigma. If she let herself she’d get attached, whether to him personally or the mystery that orbits him she’s not quite certain, so she reined herself in and doesn’t ask what he meant by her being different and changed the subject again, “Where did you learn to cook?”

This seemed to be a topic that Oliver is willing to at least give some answers to, “My nanny.” 

“Nanny? Really?” Felicity is a bit caught off guard, she’s has never met anyone who ever had a nanny.

“Her official title was head housekeeper, but she was much more than that.” 

“How much money do you have?” Felicity’s eyes bugged out a little bit as she caught her faux pas but Oliver’s only response is a raised eyebrow and he doesn’t seem to insulted by her. 

Before she can even retract what she said he answered, “A lot.” 

“I am really bad about this morning after stuff,” she mumbled towards the ceiling, debating again whether she should just give up and walk right out the door. The french toast smells delicious and it has to be almost done and she’s fairly certain she can stop putting her foot in her mouth once she can replace it with food. Maybe she has her priorities mixed up and maybe this isn’t one-night stand protocol but neither she nor her mother cook and in a couple of days she’ll be back at MIT where she will be studying her ass off and only eating when she actually remembers. 

“What are you always reading at the bar?” 

“Usually articles on developing tech. Or things from my course list.” 

“Course list?”

“Yeah, I’m currently on break from MIT.” 

“Oh.” She can’t decide if he’s impressed by this piece of information or turned off by it. A number of men in her past have walked away from her because she was smarter than them and that made them uncomfortable. Oliver could easily be one of those men. Instead of making any other comments on it, he returned to the French toast, dusting the stack on the plate with powdered sugar before he set it in front of her. “Enjoy.” 

Once the plate was in front of her Felicity dug in voraciously, the moan escaped her mouth before it became a conscious thought. Felicity immediately slapped a hand over her mouth as her eyes darted to Oliver. His smirk was back in full force, “It’s good to know that my food can bring you as much enjoyment as our time together last night.” 

Felicity felt the blush rise on her face but knew that now the conversation was brought up again she couldn’t move passed it again, “So, about last night,” Oliver nodded his consent while taking another bite of his breakfast so she powered through the rest of her statement, “it was good.” As his raised eyebrow she added, “really good. And I was wondering if maybe you’d…” Felicity forced the rest of the statement out because she knew if she stopped she would never say it, “wanttotrythisagainsometime.” 

Felicity had been watching his face from where she sat as she pressed out her words. Oliver stared straight past her revealing none of his thoughts. Felicity looked at the clock on the oven behind him and wondered when she should break the tension that was bound to turn awkward if she left it much longer. It was then that she saw as Oliver slowly started to nod his head like it wasn’t the prospect of her that had slowed his decision but his own internal debate. “I think I’d like that.” 

The smile on Oliver’s face as he refocused his eyes on her would not be easily forgotten.

**Notes for the Chapter:**

> All publicly recognizable characters, settings, etc. are the property of their respective owners. The original characters and plot are the property of the author of this story. The author is in no way associated with the owners, creators, or producers of any previously copyrighted material. No copyright infringement is intended.


	8. Chapter 8

**Notes for the Chapter:**

> Oh, would you look at that, an update. Thanks for taking the time to read my work!

Oliver looked over at his alarm clock for the sixth time within the last 45 minutes. He hasn’t been able to calm his mind down since he laid down. It seemed pointless to stay in bed when there were other things he could be doing and better ways to keep his mind from his problems. 

After showering and writing a note for Thea when she wakes, he heads to the garage grabbing the Ducati hoping it will help him focus his mind. 

The lights are on, as they should be, when he arrives at the bakery, meaning Sara has already started prepping for the morning rush. 

It wasn’t always his dream to open a bakery but in the last couple of years, he has needed something to fill his time. Medvezhonok Bakery, four blocks from QC, was the perfect location. It was close enough to his family legacy that he could easily walk there when the board needed his opinion on something and far enough away that this mother wasn’t always breathing down his neck for the choices he made. Baking had always been his way to deal with stress and it was an easy way to bring joy to the lives of the people he loved. 

He debates sneaking in through the back to start experimenting with new recipes but no matter how he enters he’ll get confronted eventually, all he’d be doing is putting it off. He’s never been called a coward so he enters through the front where he sees Roy taking down chairs and wiping off tables getting ready to open. Roy quirked his eyebrow in surprise but made no comment at Oliver’s unexpected appearance. That’s what Oliver always liked about Roy, his ability to keep his mouth shut during the early hours of the morning. Roy’s presence in the front means that Sara will still be in the back putting finishing touches on some of their sweet confections. 

Oliver passed through the swinging doors and headed straight to the sink to wash his hands knowing that Sara would start her inquisition at any moment. 

“I thought you weren’t working this morning.” Her voice doesn't sound suspicious, merely stating a fact, but Oliver knows better than to let his guard down around her. 

“I changed my mind.”

“It doesn’t have anything to do with your ex-girlfriend showing up at the casino last night?” Oliver’s shoulders tensed as he dried his hands, “Dig texted last night and gave me a heads up, said we might see you here this morning.” Sara paused as if she expected him to say something. “I owe him 20 bucks, I figured you’d drink your sorrows, Dig said you’d bake. Damn him for always being right.” 

“What else do you need prepped this morning?” Oliver finally looked to Sara, her face was hard but she then rolled her eyes and turned back to her work. 

“A daily special. There’s bananas on the counter that need to be used.” 

Oliver walked over to his prep station and started gathering all the supplies he would need. When he had all of the basic ingredients, he couldn’t help but glare at the bananas. He had come to work in order to forget his recent run-in but that was not in the cards. 

Oliver grabbed the rest of the supplies he needed for banana bread recipe he had been tweaking. He grabbed the chocolate chips in the fridge along with the cream cheese, milk, and sour cream. He stared at the walnuts in the drawer far longer than he should have. As a general rule, he avoided cooking with them. Today it wouldn’t matter whether he used them or not his mind would still be on her. 

In the last year and a half, he was getting very good at not thinking about her. Psychologists would probably say that his avoidance of the topic was not healthy but many of Oliver’s habits were unhealthy. 

Tonight, he even has a date. A date that he isn’t very excited about, especially after his run-in with her. He had been told multiple times that it was past time to move on and he has had a few dalliances but nothing serious. Tonight is meant to be an effort to move on to something more serious, an actual date, with dinner, and no sex. Well, no sex had been the plan before last night but this morning after seeing her again for the first time in five years his skin felt a little too tight in places. The reckless need that coursed through his veins for years when he was younger seems to be trying to peek out of its forced hibernation. Recklessness sounds good to him which usually means terrible life decisions that affect him and his entire family. 

Oliver smashed the bananas with a little more force than was probably needed. 

“So are you going to be all broody and annoying all day then?” Sara has gotten out some modeling chocolate and she’s perfecting flowers for a wedding cake they’re designing. 

Oliver rolled his eyes. His back was to Sara so she couldn’t see his initial reaction though he’s sure she knows what it is. He hates when he is called broody but on days like this, he has to admit that the description fits.

Falling into the routine saves him from his own thoughts. He knows the recipe backward and forwards but he’s tripling it today and wants to get it perfect. 

It’s not the first time that baking has brought him back into himself. If the alternative is beating the shit out of someone or bloodying his hands until he can barely move his fingers he’ll take flour on his brow every time. It centers him in a way that few things ever have. At first, it was the math and the chemistry, two things that he was never great at when he was younger, that kept his mind focused enough when he had a disagreement with his father or a fight with a girlfriend or fuck buddy. Once he had a better mastery of the chemistry his mind wandered to figuring out how to make the recipe better. What would happen if he added crushed pistachios to the cake? Would sour cream make it more moist than butter? Even in the depths of his darkest days, baking was the release valve. 

The smell of brown sugar reminds him of Raisa, she was the one who introduced him to all things in the kitchen. Watching sitcoms growing up he looked to the perfect mom’s cooking for their children and then eating around the table. That was never the Queen household. The Bratva made sure of that. 

Oliver didn’t know that his family was a part of the Russian mob growing up. He knew that his life was different than all of the others at Starling Prep but in his youthful ignorance he assumed it was because of his family’s wealth. When his father sent him to martial arts training at the age of six he assumed it was because his father’s bodyguards wouldn’t always be around and it was important he knew how to protect himself. 

He once asked his mother what her favorite thing to make in the kitchen was, he received a 40-minute lecture about the importance of women in the workplace. He never mentioned it to her again. 

When he asked Rasia that same question she smiled at him and held his cheek and answered, “Anything that reminds me of home, sweet boy, but pryaniki is my favorite.” It turned out that pryaniki would become Oliver’s favorite as well, making and eating. 

He’d made it once for her and she pulled her nose at it. He stared at her in disbelief and her smile was unbelievable when he mentioned to her that they were his favorite. “Of course they’re your favorite,” she had replied, “spicy but full of sweetness.” 

No one ever talked to him the way that she did. 

He can’t believe that she is back in his life. It doesn’t matter that the moment lasted less than twenty minutes she was still there, standing in front of him, as beautiful as ever. On his dark days, he daydreams about her. He wonders what she’s up to, where she’s working, if she’s happy. On his darkest of days, he hopes that she isn’t happy, that she’ll use her phenomenal hacking skills and try to find him and then they could be together again, happy. 

That was a dream for fools though, a dream he hadn’t had in eight months at the bare minimum. Of course, she lived in Starling now. If it wasn’t for bad luck he wouldn’t have any luck at all.

**Notes for the Chapter:**

> Recipe that is being referenced above: http://carlsbadcravings.com/cream-cheese-stuffed-chocolate-chip-banana-coffee-cake-recipe/?crlt.pid=camp.jjb2jUb1NqjZ#

**Author's Note:**

> This is a work in progress and also my first fic I have posted. I hope to update soon but make no promises. I have a few chapters already written but they still need to be edited. Thanks for reading!


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